A NEW APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE PSEUDO-SUGAR AND PSEUDO-NUCLEOSIDE -SYNTHESES OF PSEUDO-α-D-ARABINOFURANOSE, (+)-CYCLARADINE, AND (+)-1, PSEUDO-β-D-ARABINOFURANOSYLURACIL FROM D-ARABINOSE -

Abstract

An optically active pseudo-sugar, pseudo-α-D-arabinofuranose, was synthesized from D-arabinose in favorable overall yield by using a stereoselective formation of branched nitropyranose as the key step.Furthermore, two biologically active pseudo-β-D-arabinofuranosylnuleosides, (+)-cyclaradine and (+)-1-pseudo-β-D-arabinofuranosyluracil, were synthesized via Michael-type reactions of nucleic acid bases and a nitrocyclopentene derivative which was prepared from a synthetic intermediate of pseudo-D-arabinofuranose.